Azo compounds having a 2-acyloxy-, alkoxy-, substituted alkoxy-or hydroxy-3-alkynyloxy or substituted alkenyloxy-propyl group

ABSTRACT

Compounds of the formula ##STR1## wherein D is a diazo component radical, 
     K is the radical of a coupling component of the 1,4-phenylene or 1,4-naphthylene series, 
     R 1  is hydrogen; alkyl; or alkenyl; and when K is a coupling component radical of the 1,4-phenylene series, R 1  is also alkenyl monosubstituted by halogen; or alkyl which is substituted by a halogen, hydroxy, alkoxy, acyloxy, phenyl, phenoxy, cyano, alkenyloxy, alkynyloxy or alkoxyalkynyloxy group and is optionally further substituted by a hydroxy group, 
     R 2  is hydrogen, acyl, alkyl or alkyl monosubstituted by halogen, alkoxy, phenyl, phenoxy, benzyloxy, hydroxy or acyloxy and ##STR2##  with the proviso that when R 4  is ##STR3##  K is a coupling component radical of the 1,4-naphthylene series, R 5  is hydrogen, or ##STR4##  each of R 3  and R 3  &#39; is independently hydrogen or alkyl, or R 3  and R 3  &#39; together with the carbon atom to which they are bound form a cyclohexane ring, with the proviso that when R 3  and R 3  &#39; form a cyclohexane R 5  is hydrogen, 
     one of 
     R 6  and R 6  &#39; is hydrogen and the other is hydrogen or halogen, 
     R 7  is hydrogen or alkyl, 
     each of 
     R 8  and R 8  &#39; independently, is hydrogen or alkyl and 
     R 9  is hydrogen, acyl, alkyl or alkyl monosubstituted by alkoxy, alkoxyalkoxy or acyloxy, 
     wherein all alkyl and alkoxy moieties contain 1 to 6 carbon atoms, and all alkenyl and alkynyl moieties contain 2-6 carbon atoms, which compounds are useful as disperse dyes for dyeing or printing substrates comprising synthetic or semi-synthetic, hydrophobic, high molecular weight organic textile materials.

This application is a continuation-in-part of application Ser. No. 940,800, filed September 5, 1978 and now abandoned.

The present invention relates to azo compounds, their production and use as disperse dyes.

More particularly, the present invention provides azo disperse dyes of formula I, ##STR5## in which D is a diazo component radical,

K is the radical of a coupling component of the 1,4-phenylene or 1,4-naphthylene series,

R₁ is hydrogen; alkyl; or alkenyl; and when K is a coupling component radical of the 1,4-phenylene series, R₁ may also be alkenyl monosubstituted by halogen; or alkyl which is substituted by a halogen, hydroxy, alkoxy, acyloxy, phenyl, phenoxy, cyano, alkenyloxy, alkynyloxy or alkoxyalkynyloxy group and is optionally further substituted by a hydroxy group,

R₂ is hydrogen, acyl, alkyl or alkyl monosubstituted by halogen, alkoxy, phenyl, phenoxy, benzyloxy, hydroxy or acyloxy,

R₄ is ##STR6## with the proviso that when R₄ is ##STR7## K is a coupling component radical of the 1,4-naphthylene series, R₅ is hydrogen or ##STR8## each of R₃, and R₃ ' independently, is hydrogen or alkyl, or R₃ and R₃ ' together with the carbon atom to which they are bound form a cyclohexane ring, with the proviso that when R₃ and R₃ ' form a cyclohexane ring R₅ is hydrogen,

one of

R₆ and R₆ ' is hydrogen and the other is hydrogen or halogen,

R₇ is hydrogen or alkyl,

each of

R₈ and R₈ ', independently, is hydrogen or alkyl and

R₉ is hydrogen, acyl, alkyl or alkyl monosubstituted by alkoxy, alkoxyalkoxy or acyloxy,

wherein all alkyl and alkoxy moieties contain 1 to 6, preferably 1 to 4, more preferably (1 or 2 carbon atoms and all alkenyl and alkynyl moieties contain 2 to 6, preferably 2 to 4, more preferably 2 or 3, carbon atoms.

By halogen as used herein is meant chlorine, bromine, fluorine or iodine.

The preferred halogens are chlorine, bromine and iodine, with chlorine and bromine being most preferred.

By acyl as used herein is meant radicals of the formula R--Y-- or R'--Y--, in which

R is C₁₋₆ (preferably C₁₋₂)alkyl, halo-C₁₋₆ -(preferably C₁₋₂)alkyl, β- or γ-hydroxypropyl, β, γ-dihydroxypropyl, phenyl, tolyl or benzyl,

X is --O--CO-- in which R is bound to the oxygen atom or --SO₂ --,

R' is hydrogen or has one of the significances of R,

Y is --CO--, --NR"CO-- or --NR"--SO₂ -- in which R' is bound to the nitrogen atom, and

R" is hydrogen or has one of the significances of R.

Acyloxy is to be understood accordingly.

The diazo component radical D may be any of those common in disperse dyestuffs and may be of the benzene, naphthalene or heterocyclic series, which diazo component radicals are radicals of monoazodiazo components or of polyazo (preferably disazo) diazo components free from sulpho, carboxy and catonic groups.

Preferred diazo component radicals are those of the benzene, benzothiazolyl, benzisothiazolyl, thienyl, thiazolyl or thiadiazolyl series, with those of the benzene series, especially radicals of monoazo or disazo components, being most preferred. Preferably, D is D', where D' is phenyl which is optionally substituted by a total of up to 4 substituents selected from the group consisting of chlorine, bromine (up to 4 of each of these), cyano, iodine, trifluoromethyl, (C₁₋₂)alkylsulphonyl, nitro, methyl, methoxy (up to 2 of each of these), phenylaminocarbonyl, formyl, alkyl(C₁₋₄)carbonyl, alkoxy(C₁₋₂)carbonyl, aminocarbonyl, (C₁₋₂)-alkylaminocarbonyl, di-(C₁₋₂)alkylaminocarbonyl, phenyl, benzoyl, benzylcarbonyl, phenylsulphonyl, tolylsulphonyl, aminosulphonyl, (C₁₋₂)alkylaminosulphonyl, (C₁₋₂ alkyl)carbonylamino, thiocyano, di(C₁₋₂)alkylaminosulphonyl and phenylazo (up to one of each of these) the phenyl of which phenylazo group is optionally substituted by up to three substituents selected from chlorine, bromine (up to three of each of these), methyl, (C₁₋₂)alkoxy, cyano, nitro (up to two of each of these) and phenyl (up to one thereof); benzothiazolyl which is optionally substituted by a total of up to two substituents selected from the group consisting of chlorine, bromine, cyano, nitro (up to two of each of these), methyl, (C₁₋₂)alkylsulphonyl, aminosulphonyl and thiocyano (up to one of each of these); benzisothiazolyl which is optionally substituted by a total of up to two substituents selected from the group consisting of chlorine, bromine, cyano (up to two of each of these), nitro and (C₁₋₂)alkylsulphonyl (up to one of each of these); thienyl which is optionally substituted by a total of up to three substituents selected from the group consisting of chlorine, bromine, cyano, nitro (up to two of each of these), methyl, phenyl, alkyl(C₁₋₃)carbonyl, hydroxy and methoxycarbonyl (up to one of each of these); thiazolyl which is optionally substituted by a total of up to two substituents selected from the group consisting of chlorine, bromine, cyano (up to two of each of these), methyl, nitro and (C₁₋₂)alkylsulphonyl (up to one of each of these); 3-phenyl-1,2,4-thiadiazolyl(5); or 2-phenyl-1,3,4-thiadiazolyl(5).

More preferably D is D", where D" is phenyl which is optionally substituted by a total of up to three substituents selected from the group given above.

Even more preferably D is D"', where D"'is phenyl which is optionally substituted by a total of up to three substituents selected from chlorine, bromine, iodine, nitro, cyano, (C₁₋₂)-alkylsulphonyl (up to two of each of these), aminosulphonyl, alkoxy(C₁₋₂)carbonyl and di(C₁₋₂)alkylaminosulphonyl (up to one of each of these).

Most preferably D is D^(IV), where D^(IV), is a group of the formula ##STR9## in which R₁₂ is hydrogen, chlorine, bromine, iodine, nitro, cyano, (C₁₋₂)alkylsulphonyl or alkoxy(C₁₋₂)carbonyl,

R₁₃ is nitro, aminosulphonyl or di(C₁₋₂)alkylaminosulphonyl,

R₁₄ is hydrogen, chlorine, bromine, iodine, cyano or (C₁₋₂)alkylsulphonyl, and

R₁₄ ' is hydrogen or when R₁₄ is hydrogen, R₁₄ ' is hydrogen, chlorine or bromine.

Preferably R₁₂ is R₁₂ ', and where R₁₂ ' is nitro or cyano. Preferably R₁₃ is nitro. Preferably R₁₄ is R₁₄ " where R₁₄ " is chlorine, bromine, cyano or methylsulphonyl and R₁₄ ' is hydrogen.

Preferably K is K', where K' is unsubstituted 1,4-naphthylene or a group of formula II ##STR10## in which R₁₀ is hydrogen, chlorine, bromine, (C₁₋₂)-alkyl, (C₁₋₂)alkoxy, β-hydroxyethoxy,, β-methoxyethoxy or cyano(C₁₋₂)alkoxy,

R₁₁ is hydrogen, chlorine, bromine, (C₁₋₂)alkyl, (C₁₋₂)alkoxy, alkyl(C₁₋₄)carbonylamino, bromo- or chloro(C₁₋₂ alkyl)carbonylamino e.g. bromo- or chloroethylcarbonylamino, cyano, formylamino, alkoxy(C₁₋₂)alkyl(C₁₋₄)-carbonylamino, alkoxy(C₁₋₄)carbonylamino, phenoxyalkyl(C₁₋₂)carbonylamino, β- or γ-alkoxy(C₁₋₂)alkoxy(C₂₋₃)carbonylamino, alkoxy(C₁₋₄)carbonylalkyl(C₁₋₃)aminocarbonylamino, benzoylamino or phenylalkyl(C₁₋₂)carbonylamino, and the asterisk denotes the carbon atom attached to the azo group.

Preferably R₁₀ is R₁₀ ', where R₁₀ ' is hydrogen, (C₁₋₂)-alkoxy or β-hydroxyethoxy.

More preferably R₁₀ is R₁₀ ", where R₁₀ " is methoxy or ethoxy.

R₁₁ is preferably R₁₁ ', where R₁₁ ' is hydrogen, methyl, formylamino, alkyl (C₁₋₂)carbonylamino, chloromethylcarbonylamino, C₁₋₂ alkoxy (C₁₋₄)alkylcarbonylamino or C₁₋₄ alkoxycarbonylamino. More preferably, R₁₁ ' is alkyl(C₁₋₂)-carbonylamino, especially ethylcarbonylamino.

R₁ is preferably R₁ ', where R₁ ' is, in the case where K is a radical of the 1,4-phenylene series, hydrogen; (C₁₋₄)-alkyl; (C₂₋₄)alkyl monosubstituted in the β-, α- or δ-position by chlorine, bromine, hydroxy, (C₁₋₂)alkoxy, formyloxy, alkyl(C₁₋₄)carbonyloxy, alkoxy(C₁₋₂)carbonyloxy, (C₁₋₂)alkylaminocarbonyloxy, phenoxy, phenyl, benzoyloxy or cyano; β-hydroxy-γ-chloropropyl; benzyl, allyl, 2- or 3-chloro- or bromoallyl; --CH₂ CHOHCH₂ OCH₂ C.tbd.CH; or --CH₂ CHOHCH₂ OCH₂ --C.tbd.CCH₂ OCH₃ or R₁ ', in the case where K is 1,4-naphthylene, is hydrogen or (C₁₋₄)alkyl.

More preferably, R₁ ' is R₁ ", where R₁ ", in the case where K is 1,4-naphthylene, is hydrogen or (C₁₋₂)alkyl and, in the case where k is a radical of the 1,4-phenylene series, is hydrogen, (C₁₋₂)alkyl, β- or γ-alkyl(C₁₋₂)carbonyloxy or cyano-substituted (C₂₋₃)alkyl. Most preferably R₁ is hydrogen.

R₂ is preferably R₂ ', where R₂ ' is hydrogen; (C₁₋₄)alkyl; (C₁₋₄)alkyl monosubstituted by chlorine or bromine or (C₂₋₄)alkyl substituted in the β-, γ- or δ-position by (C₁₋₂)alkoxy, hydroxy, phenoxy, formyloxy, alkyl(C₁₋₃)carbonyloxy or benzyloxy; alkyl(C₁₋₄)carbonyl; benzoyl or alkoxy(C₁₋₄)carbonyl. More preferably R₂ is R₂ ", where R₂ " is hydrogen or (C₁₋₄), preferably (C₁₋₂), alkyl with hydrogen being most preferred.

Each of R₃ and R₃ ', independently, is preferably R_(3a) and R_(3a) ', where R_(3a) and R_(3a) ' are independently hydrogen or methyl or together form a cyclohexane ring with the proviso that R_(3a) and R_(3a) ' may form a cyclohexane ring only when R₅ is hydrogen. More preferably each of R₃ and R₃ ', independently, is hydrogen or methyl, with hydrogen being most preferred.

R₅ is preferably R₅ ', where R₅ ' is hydrogen, α-(C₁₋₂)-alkoxy(C₁₋₃)alkyl, β-methoxyethoxymethyl, acetoxymethyl or chloropropionyloxymethyl. More preferably R₅ is R₅ ", where R₅ " is hydrogen, β-methoxyethoxymethyl or acetoxymethyl, with hydrogen being especially preferred.

Each of R₆ and R₆ ', independently, is preferably R_(6a) and R_(6a) ', where each of R_(6a) and R_(6a) ' is, independently, hydrogen, chlorine or bromine, with the proviso that at least one of R_(6a) and R_(6a) ' is hydrogen. Most preferably both R₆ and R₆ ' are hydrogen.

R₇ is preferably R₇ ', where R₇ ' is hydrogen or methyl. Most preferably R₇ is hydrogen.

R₄ is preferably R₄ ', where R₄ ' is --C.tbd.C--R₅ ' or ##STR11## More preferably R₄ is R₄ ", where R₄ " is --C.tbd.C--R₅ ' or vinyl. Most preferably R₄ is --C.tbd.C--R₅ ", especially --C.tbd.C--H.

Preferred compounds of formula I are

(i) those where D is D', K is K', R₁ is R₁ ', R₂ is R₂ ', R₃ and R₃ ' are R_(3a) and R_(3a) ' and R₄ is --C.tbd.C--R₅ or ##STR12## preferably R₄ '; (ii) those of (i) but where D is D";

(iii) those where D is D", K is K', R₁ is R₁ ", R₂ is R₂ ", each of R₃ and R₃ ', independently, is hydrogen or methyl and R₄ is R₄ ';

(iv) those of (iii) where D is D'";

(v) those of (iii) where D is D^(IV), K is K', where R₁₀ and R₁₁ are R₁₀ ' and R₁₁ ', R₁ is R₁ ", R₂ is R₂ ", each of R₃ and R₃ ' is hydrogen and R₄ is R₄ ";

(vi) those of (v) where R₁ is hydrogen, R₂ is hydrogen, and R₄ is --C.tbd.C--R₅ " or vinyl;

(vii) those of (v) where R₄ is --C.tbd.C--R₅ ";

(viii) those of (vi) wherein R₁₂ is R₁₂ ', R₁₃ is nitro, R₁₄ is R₁₄ " and R₁₄ ' is hydrogen;

(ix) those of (viii) where R₄ is --C.tbd.C--R₅ ", especially those where R₄ is --C.tbd.C--H.

Other compounds of Formula I include

(i) those wherein D is D^(IV), wherein R₁₂ is R₁₂ ', R₁₃ is nitro, R₁₄ is R₁₄ " and R₁₄ ' is hydrogen, K is K', R₁ is hydrogen, R₂ is hydrogen, and R₄ is --C.tbd.C--R₅ ";

(ii) those wherein D is D', K is K' and R₄ is --C.tbd.C--R₅ ;

(iii) those wherein D is D', K is K', R₁ is R₁ ', R₂ is R₂ ', R₃ and R₃ ' are R_(3a) and R_(3a) ', respectively, and R₄ is --C.tbd.C--R₅ ';

(iv) those of formula I" ##STR13## wherein D is a diazo component radical,

K is the radical of a coupling component of the 1,4-phenylene or 1,4-naphthylene series,

R_(1a) is hydrogen; C₂₋₄ alkyl; C₂₋₄ alkenyl; C₂₋₄ alkyl monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, acyloxy, phenyl, phenoxy, cyano, alkynyloxy or alkoxyalkynyloxy; or C₂₋₄ alkyl substituted by hydroxy and one further substituent selected from the group consisting of halo, hydroxy, C₁₋₄ alkoxy, acyloxy, phenyl, phenoxy, cyano, alkynyloxy or alkoxyalkynyloxy, with the provisos that R_(1a) may be C₂₋₄ alkenyl only when K is a coupling component radical of the 1,4-naphthylene series and R_(1a) must be hydrogen, C₂₋₄ alkyl or C₂₋₄ alkenyl when K is a coupling component radical of the 1,4-naphthylene series,

R_(2a) is hydrogen, acyl, alkyl or alkyl monosubstituted by halo, C₁₋₄ alkoxy, phenoxy, phenyl, benzyloxy or acyloxy,

each of

R₃ " and R₃ "' is independently hydrogen or C₁₋₄ alkyl or

R₃ " and R₃ "' taken together and with the carbon atom to which they are joined form a cyclohexyl ring, and

R₅ is hydrogen or ##STR14## wherein each of R₈ and R₈ ' is independently hydrogen or alkyl, and

R₉ ' is hydrogen, acyl, alkyl or alkyl monosubstituted by alkoxy, acyloxy or (C₁₋₄ alkoxy)C₂₋₄ alkoxy,

with the proviso that R₅ must be hydrogen when R₃ " and R₃ "' taken together and with the carbon atom to which they are joined form a cyclohexyl ring;

(v) those of Formula Ia ##STR15## wherein R₃₀ is C₁₋₂ alkyl, 2-methoxyethyl or 2-hydroxyethyl, and

R₃₁ is hydrogen, C₁₋₂ alkyl, chloromethyl, (C₁₋₂ alkoxy)C₁₋₄ alkyl or C₁₋₄ alkoxy,

R₂ "' is hydrogen or acetyl,

R₁₂ ' is nitro or cyano, and

R_(14a) is chloro, bromo, iodo, cyano or methylsulfonyl; and

(vi) those of Formula I"' ##STR16## wherein R_(14a) ' is chloro, bromo or iodo,

R₃₀ ' is methyl or ethyl, and

R₃₁ ' is methyl or ethyl.

The present invention also provides a process for the production of compounds of formula I comprising coupling a diazotized amine of formula IV,

    D--NH.sub.2                                                IV

with a compound of formula V, ##STR17##

Coupling may be carried out in accordance with conventional methods. Diazotization of the amine of formula IV may also be carried out in accordance with known methods.

The compounds of formula IV are known.

The compounds of formula V may be prepared in accordance with conventional methods, for example by condensing a compound of formula VI,

    H--K--NHR.sub.1                                            VI

with a compunds of formula VII, ##STR18## in the presence of an acid binding agent e.g. potassium hydroxide

The compound of formula VII may be prepared by conventional methods, for example by the addition reaction of the corresponding alcohol with epichlorohydrin in the presence of boron trifluoride etherate.

The compounds of formula I are useful as disperse dyestuffs for dyeing or printing synthetic or semi-synthetic, hydrophobic, high molecular weight organic textile substrates. They are especially suitable for exhaust dyeing, pad dyeing or printing substrates which consist of or comprise linear, aromatic polyesters, cellulose 21/2 acetate, cellulose triacetate and synthetic polyamides.

The compounds of formula I may be made up into dyeing preparations in accordance with known methods, for example by grinding in the presence of dispersing agents and/or fillers, optionally with vacuum or spray drying.

Dyeing and printing may be carried out in accordance with known methods, for example as described in French Pat. No. 1,445,371.

The dyes of formula I possess notable build-up and give dyeings which have a good depth of shade. Further, the dyes give dyeings which have good sublimation fastness; the dyeings obtained by printing processes possess equally good properties to those obtained by dyeing processes.

The following Examples further serve to illustrate the invention. In the Examples all parts and percentages are by weight and all temperatures are in degrees Centigrade.

EXAMPLE 1

5.6 parts pulverised potassium hydroxide are added portionwise to a mixture of 14.3 parts α-naphthylamine and 14.85 parts, 2-hydroxy-3-chloropropyl-prop-2'-ynylether whereby the temperature rises from 25° to 50°. The mixture is stirred for 10 hours at 85° and cooled to room temperature whereupon approximately 100 parts of diluted hydrochloric acid are added thereto and the mixture is stirred for 10 minutes. The organic phase N-[3-prop-2'-ynyloxy)-2-hydroxy-propyl]-α-naphthylamine in oily form is then separated out.

8 parts of crystalline sodium nitrite are slowly added, with stirring at 60°, to 147 parts concentrated sulphuric acid. The soluton is cooled to 10°-20°, 10 parts glacial acetic acid are added thereto and after further cooling to 0°-5°, 26.2 parts of 2-bromo-4,6-dinitroaniline are added thereto. 10 parts of glacial acetic acid are added to the reaction mixture which is stirred for 3 hours at 0°-5°, the excess nitrosylsulphuric acid being decomposed with a small amount of urea. The diazonium solution so obtained is added, with stirring, to a solution of 25.5 parts of the naphthylamine coupling component, obtained as described above, in 400 parts methanol cooled to 0° to 5°. After coupling is complete, the dyestuff is precipitated out by the addition of a 36% sodium hydroxide solution, stirred for 1 hour, filtered and washed with water until acid free.

In order to improve the dyeing properties and the dispersion stability of the dye, it is added to 100 parts water, stirred for 3 hours at 90°, filtered, washed with water and dried. The dyestuff obtained of the formula ##STR19## dyes polyester fibres in blue shades.

Further dyestuffs which may be prepared in analogy with the procedure described in Example 1 are given in Tables 1 to 8.

                                      TABLE 1                                      __________________________________________________________________________      ##STR20##                                                                     __________________________________________________________________________     Example                                                                        No.  R.sub.1           R.sub.3                                                                            R.sub.3                                                                             R.sub.5    R.sub.2                             __________________________________________________________________________     2    C.sub.2 H.sub.5   H   H    H          H                                   3    C.sub.2 H.sub.4 CN                                                                               CH.sub.3                                                                           H    CHCH.sub.3 OCH.sub.3                                                                      COCH.sub.3                          4    "                 H   H    H          CH.sub.3                            5    H                 H   H    CH.sub.2OCH.sub.3                                                                         H                                   6    H                 H   H    H          H                                   7    H                 CH.sub.3                                                                           CH.sub.3                                                                            C(CH.sub.3).sub.2 OC.sub.2 H.sub.5                                                        H                                   8    C.sub.4 H.sub.9   H   H    CH.sub.2OCH.sub.3                                                                         COC.sub.6 H.sub.5                   9    H                 H   H    H          H                                   10   C.sub.2 H.sub.4 OCOCH.sub.3                                                                      H   H    CH.sub.2OC.sub.2 H.sub.5                                                                  H                                   11   C.sub.2 H.sub.5   H   H    H          COOC.sub.2 H.sub.5                  12   CH.sub.2CH.sub.2OCH.sub.3                                                                        CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     H          CH.sub.2CH.sub.2OCH.sub.3           13   C.sub.2 H.sub.4 OCOOCH.sub.3                                                                     H   H    CH.sub.2OCOCH.sub.3                                                                       CH.sub.2 CH.sub.2OC.sub.6                                                      H.sub.5                             14   H                 H   H    CH.sub.2OCOC.sub.2 H.sub.4 Cl                                                             H                                   15   CH.sub.2CHCH.sub.2                                                                               H   H    H                                                                                          ##STR21##                          16   C.sub.2 H.sub.4 OCHO                                                                             H   H    CH.sub.2OC.sub.2 H.sub.4 OCH.sub.3                                                        H                                   17   H                 H   H    CH.sub.2OCH.sub.3                                                                         H                                   18   C.sub.2 H.sub.4 OCOC.sub.4 H.sub.9                                                               H   H    H          COC.sub.4 H.sub.9                   19   H                 H   H    CH.sub.2OC.sub.2 H.sub.5                                                                  H                                   20   C.sub.2 H.sub.4 OC.sub.6 H.sub.5                                                                 CH.sub.3                                                                           CH.sub. 3                                                                           C(CH.sub.3).sub.2 OCH.sub.3                                                               H                                   21   C.sub.2 H.sub.4 Cl                                                                               H   H    CH.sub.2 OCH.sub.3                                                                        CH.sub.2CH.sub.2Cl                  22   C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                                 H   H    CH.sub.2OC.sub.2 H.sub.5                                                                  H                                   23   C.sub.2 H.sub.4 OH                                                                               H   H    H          CH.sub.2CH.sub.2Br                  24   CH.sub.2 CHOHCH.sub.2 OCH.sub.2 CCH                                                              H   H    H          H                                   25   CH.sub.2CH.sub.2OH                                                                               H   H    CH.sub.2OCH.sub.3                                                                         H                                   26   CH.sub.2C.sub.6 H.sub.5                                                                          H   CH.sub.3                                                                            CH.sub.2OCH.sub.3                                                                         H                                   27   C.sub.2 H.sub.4 Br                                                                               CH.sub.3                                                                           CH.sub.3                                                                            C(CH.sub.3).sub.2 OCH.sub.3                                                               H                                   28                                                                                   ##STR22##        H   H    CH.sub.2OCH.sub.3                                                                         H                                   29   C.sub.2 H.sub.5   H   H    H          C.sub.2 H.sub.5                     30   C.sub.2 H.sub.4 OCOC.sub.6 H.sub.5                                                               H   H    CH.sub.2OCH.sub.3                                                                         H                                   31   C.sub.2 H.sub.4OCONHCH.sub.3                                                                     H   H    "          H                                   32   CH.sub.2CH(OH)CH.sub.2 Cl                                                                        H   H    H          H                                   33   H                 H   H    H          H                                   34   C.sub.2 H.sub.5   CH.sub.3                                                                           CH.sub.3                                                                            H          "                                   35   "                 H   H    CH.sub.2OCH.sub.3                                                                         "                                   36a  H                 H   H    H          H                                   36b  H                 H   H    H          H                                   36c  H                 H   H    H          H                                   36d  H                 H   H    H          H                                   36f  H                 H   H    H          H                                   36g  H                 H   H    H          H                                   36h  H                 H   H    H          H                                   36i  H                 H   H    H          H                                   36j  H                 H   H    H          H                                   36k  H                 H   H    H          H                                   36l  H                 H   H    H          COCH.sub.3                          36m  H                 H   H    H          "                                   36n  H                 H   H    H          H                                   36o  H                 H   H    H          H                                   36p  H                 H   H    H          H                                   36q  H                 H   H    H          H                                   __________________________________________________________________________     Example                                          Shade on                      No.  R.sub.12                                                                           R.sub.11   R.sub.13  R.sub.10 R.sub.11  polyester                     __________________________________________________________________________     2    H   H          NO.sub.2  H        CH.sub.3  red                           3    Cl  H          "         H        NHCOCH.sub.3                                                                             "                             4    "   H          SO.sub.2 CH.sub.3                                                                        H        H         orange                        5    NO.sub.2                                                                           Cl         NO.sub.2  OC.sub.2 H.sub.5                                                                        NHCOCH.sub.3                                                                             blue                          6    "   Br         "         OCH.sub.3                                                                               "         "                             7    NO.sub.2                                                                           CN         "         OC.sub.2 H.sub.5                                                                        NHCOC.sub.2 H.sub.5                                                                      "                             8    "   SO.sub.2 CH.sub.3                                                                         "         OCH.sub.3                                                                               CH.sub.3  "                             9    CN  H          "         "        "         violet                        10   Cl  Cl         NO.sub.2  H        Cl        brown                         11   H   H          C.sub.6 H.sub.5NN                                                                        H        H         scarlet                       12   Br  Br         CONH.sub.2                                                                               H        C.sub.2 H.sub.5                                                                          brown                         13   Cl  H          SO.sub.2 CH.sub.3                                                                        H        NHCOCH.sub.3                                                                             red                           14   Cl  H          CON(C.sub.2 H.sub.5).sub.2                                                               OCH.sub.3                                                                               H         orange                        __________________________________________________________________________     Example                                          Shade on                      No.  R.sub.12                                                                           R.sub.14   R.sub.13  R.sub.10 R.sub.11  polyester                     __________________________________________________________________________     15   CN                                                                                  ##STR23## NO.sub.2  H        CH.sub.3  blue                          16   H   CF.sub.3   "         CH.sub.3 "         red                           17   NO.sub.2                                                                           I          "         OC.sub.2 H.sub.4OCH.sub.3                                                               NHCOC.sub.2 H.sub.4 Cl                                                                   blue                          18   Br  CN         "         OC.sub.2 H.sub.5                                                                        CH.sub.3  "                             19   CN  SO.sub.2 CH.sub.3                                                                         "         OCH.sub.3                                                                               NHCOCH.sub.3                                                                             "                             20   Cl  H          CONHCH.sub.3                                                                             H        H         orange                        21   Br  COOCH.sub.3                                                                               NO.sub.2  H        CH.sub.3  red                           22   Br  H          SO.sub.2 NHCH.sub.3                                                                      H        NHCOC.sub.2 H.sub.4 Cl                                                                   "                             23   Cl  H          CON(CH.sub.3).sub.2                                                                      H        H         orange                        24   Cl  H          CONHC.sub.6 H.sub.5                                                                      H        H         "                             25   Cl  H          C.sub.6 H.sub.5                                                                          H        CH.sub.3  red                           26   Cl  H          SO.sub.2 NH.sub.2                                                                        H        H         orange                        27   H   SCN        NO.sub.2  OCH.sub.3                                                                               CH.sub.3  violet                        28   H   COC.sub.6 H.sub.5                                                                         "         "        H         red                           29   CH.sub.3                                                                           COCH.sub.3 NO.sub.2  H        H         "                             30   Cl  COCH.sub.2 C.sub.6 H.sub.5                                                                "         H        Cl        "                             31   Br  H          "         H        H         "                             32   Cl  H          NO.sub.2  H        H         "                             __________________________________________________________________________     Example                                          Shade on                      No.  R.sub.12                                                                           R.sub.11   R.sub.13  R.sub.10 R.sub.11  polyester                     __________________________________________________________________________     33   H   H          COCH.sub.3                                                                               H        H         yellow                        34   H   H          COC.sub.6 H.sub.5                                                                        H        Cl        "                             35   Cl  COC.sub.4 H.sub.9                                                                         NO.sub.2  H        CH.sub.3  "                             36a  NO.sub.2                                                                           Cl         "         OC.sub.2 H.sub.5                                                                        NHCOCH.sub.3                                                                             blue                          36b  "   I          "         "        "         "                             36c  "   Br         "         "        NHCOC.sub.2 H.sub.5                                                                      "                             36d  "   Cl         "         "        "         "                             36f  "   I          "         "        "         "                             36g  "   Cl         "         OCH.sub.3                                                                               NHCOCH.sub.3                                                                             "                             36h  "   I          "         "        "         "                             36j  "   Br         "         "        NHCOC.sub.2 H.sub.5                                                                      "                             36j  "   Cl         "         "        "         "                             36k  "   I          "         "        "         "                             36l  "   Br         "         OC.sub.2 H.sub.5                                                                        NHCOCH.sub.3                                                                             "                             36m  "   Cl         "         OCH.sub.3                                                                               "         "                             36n  CN  CN         "         H        "         "                             36o  "   "          "         OCH.sub.3                                                                               CH.sub.3  "                             36p  "   NO.sub.2   "         OC.sub.2 H.sub.5                                                                        NHCOCH.sub.3                                                                             "                             36q  Br  CN         "         "        "         "                             __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR24##                                                                     __________________________________________________________________________     Example                                                                        No.  R.sub.1   R.sub.3                                                                            R.sub.3                                                                            R.sub.5 R.sub.2                                                                              R.sub.12                                  __________________________________________________________________________     37   C.sub.2 H.sub.5                                                                          H   H   H       H     Cl                                        38   H         H   H   CH.sub.2OCH.sub.3                                                                      "     Cl                                        39   C.sub.2 H.sub.4 OCOC.sub.6 H.sub.5                                                       H   H   "       "     NO.sub.2                                  40   C.sub.2 H.sub.4 OCOOCH.sub.3                                                             H   H   H       COC.sub.6 H.sub.5                                                                    CH.sub.3                                  41   H         CH.sub.3                                                                           CH.sub.3                                                                           H       COCH.sub.3                                                                           OCH.sub.3                                 42   C.sub.4 H.sub.9                                                                          H   H   CH.sub.2OCH.sub.3                                                                      "     Cl                                        43   C.sub.3 H.sub.7                                                                          H   H   H       "     OCH.sub.3                                 __________________________________________________________________________     Example                              Shade on                                  No.  R.sub.14 '                                                                              R.sub.13 R.sub.10                                                                            R.sub.11 polyester                                 __________________________________________________________________________     37   Cl       NO.sub.2 H    NHCOCH.sub.3                                                                            red                                       38   Cl       SO.sub.2 N(CH.sub.3).sub.2                                                              H    CH.sub.3 "                                         39   NHCOCH.sub.3                                                                            NO.sub.2 OC.sub.2 H.sub.5                                                                    NHCOCH.sub.3                                                                            blue                                      40   CH.sub.3 "        H    CH.sub.3 red                                       41   OCH.sub.3                                                                               "        H    Cl       "                                         42   Cl       "        OCH.sub.3                                                                           CH.sub.3 violet                                    43   CH.sub.3 "        H    "        red                                       __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR25##                                                                     Example                                        Shade on                        No.  R.sub.1                                                                             R.sub.3                                                                            R.sub.3                                                                            R.sub.2                                                                              R.sub.5  R.sub.12                                                                           R.sub.14                                                                             R.sub.13                                                                           polyester                       __________________________________________________________________________     44   H    H   H   COCH.sub.3                                                                           H        NO.sub.2                                                                           Cl    NO.sub.2                                                                           blue                            45   H    H   H   H     CH.sub.2OCH.sub.3                                                                       Br  CN    "   "                               46   H    CH.sub.3                                                                           CH.sub.3                                                                           "     H        I   NO.sub.2                                                                             "   "                               47   C.sub.2 H.sub.5                                                                     H   H   "     CH.sub.2OCH.sub.3                                                                       NO.sub.2                                                                           Br    "   "                               48   C.sub.4 H.sub.9                                                                     H   H   "     "        CN  SO.sub.2 CH.sub.3                                                                    "   "                               49   "    H   H   "     H        "   CN    "   "                               50   H    CH.sub.3                                                                           CH.sub.3                                                                           COCH.sub.3                                                                           C(CH.sub.3).sub.2 OCH.sub.3                                                             NO.sub.2                                                                           Br    "   "                               __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________      ##STR26##                                                                     __________________________________________________________________________     Example                                                                        No.  R.sub.1  R.sub.3                                                                            R.sub.3                                                                            R.sub.2                                                                               R.sub.5                                           __________________________________________________________________________     51   C.sub.2 H.sub.4 CN                                                                      H   H   H      H                                                 52   C.sub.2 H.sub.4 OCOCH.sub.3                                                             H   H   H      CH.sub.2 OCH.sub.3                                53   H        H   H   COCH.sub.3                                                                            H                                                 54   H        H   H   COC.sub.4 H.sub.9                                                                     CH.sub.2OCH.sub.3                                 55   C.sub.4 H.sub.9                                                                         CH.sub.3                                                                           CH.sub.3                                                                           C.sub.4 H.sub.9                                                                       H                                                 56   C.sub.2 H.sub.5                                                                         H   H   C.sub.2 H.sub.5                                                                       CH.sub.2OCOCH.sub.3                               57   C.sub.2 H.sub.4 CN                                                                      CH.sub.3                                                                           CH.sub.3                                                                           H      C(CH.sub.3).sub.2 OCH.sub.3                       58   H        H   H   H      H                                                 59   H        H   H   H      H                                                 60   C.sub.2 H.sub.5                                                                         H   H   H      CH.sub.2OCH.sub.3                                 61   H        H   H   H      H                                                 62   C.sub.2 H.sub.5                                                                         H   H   COOC.sub.4 H.sub.9                                                                    CH.sub.2OC.sub.2 H.sub.5                          63   H        CH.sub.3                                                                           CH.sub.3                                                                           H      C(CH.sub.3).sub.2 OCH.sub.3                       64   C.sub.2 H.sub.4 OH                                                                      H   H   H      CH.sub.2OCOCH.sub.3                               __________________________________________________________________________     Example                          Shade on                                      No.   R.sub.22                                                                            R.sub.23                                                                              R.sub.10                                                                             R.sub.11 polyester                                     __________________________________________________________________________     51    H    CN     H     NHCOCH.sub.3                                                                            red                                           52    H    SO.sub.2 CH.sub.3                                                                     H     CH.sub.3 "                                             53    NO.sub.2                                                                            NO.sub.2                                                                              OC.sub.2 H.sub.5                                                                     NHCOCH.sub.3                                                                            blue                                          54    Cl   CN     H     "        violet                                        55    H    NO.sub.2                                                                              OCH.sub.3                                                                            CH.sub.3 "                                             56    H    Cl     H     CH.sub.3 red                                           57    H    SO.sub.2 NH.sub.2                                                                     H     NHCOCH.sub.3                                                                            "                                             58    H    SCN    OC.sub.2 H.sub.5                                                                     "        blue                                          59    Cl   Cl     H     Cl       red                                           60    H    SO.sub.2 C.sub.2 H.sub.5                                                              OCH.sub.3                                                                            CH.sub.3 "                                             61    Br   Cl     H     H        "                                             62    Br   Br     H     H        "                                             63    CH.sub.3                                                                            CN     H     Cl       "                                             64    CN   CN     H     NHCOCH.sub.3                                                                            "                                             __________________________________________________________________________

                                      TABLE 5                                      __________________________________________________________________________      ##STR27##                                                                     Ex-                                                        Shade               am-                                                        on                  ple                                                        poly-               No.                                                                               R.sub.1  R.sub.3                                                                            R.sub.3                                                                            R.sub.2                                                                              R.sub.5   R.sub.24                                                                           R.sub.15                                                                             R.sub.10                                                                            R.sub.11                                                                               ester               __________________________________________________________________________     65 H        H   H   H     H         H   NO.sub.2                                                                             H    NHCOCH.sub.3                                                                           blue                66 H        H   H   COCH.sub.3                                                                           CH.sub.2OCH.sub.3                                                                        CH.sub.3                                                                           "     OC.sub. 2 H.sub.5                                                                   "       "                   67 C.sub.2 H.sub.5                                                                         H   H   "     H         Cl  Cl    H    CH.sub.3                                                                               "                   68 H        H   H   "     CH.sub.2OCOCH.sub.3                                                                      Br  Br    OC.sub.2 H.sub.5                                                                    NHCOCH.sub.3                                                                           "                   69 H        CH.sub.3                                                                           CH.sub.3                                                                           H     CH.sub.2OCH.sub.3                                                                        Cl  NO.sub.2                                                                             OCH.sub.3                                                                           CH.sub.3                                                                               "                   70 H        H   H   H     H         Br  CN    H    Cl      "                   71 C.sub.2 H.sub.5                                                                         H   H   H     H         H   SO.sub.2 C.sub.2 H.sub.5                                                             H    CH.sub.3                                                                               "                   72 C.sub.2 H.sub.4 OCOCH.sub.3                                                             H   H   H     H         CN  CN    OCH.sub.3                                                                           "       "                   __________________________________________________________________________

                                      TABLE 6                                      __________________________________________________________________________      ##STR28##                                                                     __________________________________________________________________________     Example                                                                        No.  R.sub.1                                                                              R.sub.3                                                                            R.sub.3                                                                            R.sub.5   R.sub.2                                                                              R.sub.19                                    __________________________________________________________________________     73   H     H   H   H         H     COOCH.sub.3                                 74   H     H   H   H         H     CN                                          75   H     H   H   CH.sub.2OCH.sub.3                                                                        H     CN                                          76   C.sub.2 H.sub.5                                                                      H   H   CH.sub.2OC.sub.2 H.sub.5                                                                 H     CN                                          77   "     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2OCH.sub.3                                                                        COCH.sub.3                                                                           NO.sub.2                                    78   C.sub.2 H.sub.4 OH                                                                   H   H   H         COC.sub.3 H.sub.7                                                                     OH                                         79   H     H   H   H         COC.sub.4 H.sub.9                                                                    Cl                                          80   C.sub.2 H.sub.4 Cl                                                                   H   H   CH.sub.2OCH.sub.3                                                                        H     Br                                          81   H     H   H   H         H     COC.sub.2 H.sub.5                           82   C.sub.2 H.sub.5                                                                      CH.sub.3                                                                           H   CH.sub.2OCOCH.sub.3                                                                      H     COC.sub.3 H.sub.7                           __________________________________________________________________________               Example                    Shade on                                            No.  R.sub.20                                                                            R.sub.21                                                                           R.sub.10                                                                            R.sub.11                                                                               polyester                                 __________________________________________________________________________               73   CH.sub.3                                                                            CN  OC.sub.2 H.sub.5                                                                    NHCOCH.sub.3                                                                           blue                                                74   H    NO.sub.2                                                                           H    H       red                                                 75   CH.sub.3                                                                            CN  OC.sub.2 H.sub.5                                                                    NHCOCH.sub.3                                                                           blue                                                76   C.sub.6 H.sub.5                                                                     NO.sub.2                                                                           H    Cl      red                                                 77   CH.sub.3                                                                            NO.sub.2                                                                           OCH.sub.3                                                                           CH.sub.3                                                                               violet                                              78   CH.sub.3                                                                            H   H    H       red                                                 79   Cl   H   H    CH.sub.3                                                                               "                                                   80   Br   H   H    CH.sub.3                                                                               "                                                   81   Cl   H   H    NHCOCH.sub.3                                                                           red                                                 82   Br   H   H    Cl      "                                         __________________________________________________________________________

                                      TABLE 7                                      __________________________________________________________________________      ##STR29##                                                                     __________________________________________________________________________     Example                                                                        No.  R.sub.1  R.sub.3                                                                             R.sub.3                                                                             R.sub.5  R.sub.2                                       __________________________________________________________________________     83   C.sub.2 H.sub.4 OCOCH.sub.3                                                             H    H    H        H                                             84   C.sub.2 H.sub.5                                                                         H    H    CH.sub.2OCH.sub.3                                                                       "                                             85   H        H    H    H        "                                             86   C.sub.2 H.sub.4 OH                                                                      H    H    H        "                                             87   H        H    CH.sub.3                                                                            CH.sub.2OC.sub.2 H.sub.5                                                                "                                             88   C.sub.4 H.sub.9                                                                         CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.2OCH.sub.3                                                                        COCH.sub.3                                   89   H        H    H    H        "                                             __________________________________________________________________________     Example                           Shade on                                     No.  R.sub.16                                                                             R.sub.17                                                                           R.sub.18                                                                            R.sub.10                                                                            R.sub.11 polyester                                    __________________________________________________________________________     83   Br    H   Br   H    NHCOCH.sub.3                                                                            blue                                         84   Cl    H   Cl   OCH.sub.3                                                                           CH.sub.3 "                                            85   Cl    H   CN   H    "        "                                            86   H     Br  H    H    NHCOC.sub.2 H.sub.4 Cl                                                                  "                                            87   SO.sub.2 C.sub.2 H.sub.5                                                             H   H    H    CH.sub.3 "                                            88   CN    H   CN   OCH.sub.3                                                                           CH.sub.3 "                                            89   H     H   NO.sub.2                                                                            OCH.sub.3                                                                           CH.sub.3 "                                            __________________________________________________________________________

                                      TABLE 8                                      __________________________________________________________________________     Example                                           Shade on                     No.                                               polyester                    __________________________________________________________________________     90                                                                                   ##STR30##                                   blue                         91                                                                                   ##STR31##                                   "                            92                                                                                   ##STR32##                                   red                          93                                                                                   ##STR33##                                   blue                         94                                                                                   ##STR34##                                   red                          95                                                                                   ##STR35##                                   "                            96                                                                                   ##STR36##                                   "                            97                                                                                   ##STR37##                                   "                            __________________________________________________________________________

EXAMPLE 98

14.3 parts α-naphthylamine and 11.4 parts allylglycidylether are stirred for 10 hours at 80°. The mixture is cooled to room temperature and 50 parts dilute hydrochloric acid are added thereto whereupon the mixture is stirred for about 10 minutes and the organic phase, N-(3-allyloxy-2-hydroxypropyl)-α-naphthylamine, is separated.

26.2 parts 2-bromo-4,6-dinitro-aniline are added to a mixture (prepared at a temperature under 20°) of 122 parts concentrated sulphuric acid and 35 parts 4% nitrosylsulphuric acid keeping the temperature under 20° and the mixture was stirred for 3 hours. The solution obtained, with stirring and cooling to 0° to 5°, is added dropwise to 25.7 parts of the coupling component, prepared as described above, dissolved in 100 parts methanol. After coupling is complete, the dyestuff is precipitated with 30% sodium hydroxide, stirred for 1 hour, filtered and washed free from acid. The dye is then added to 100 parts water, stirred at 90° for 2 hours, filtered, washed with water and dried. The dyestuff is obtained of the formula ##STR38## dyes polyester fibres in blue shades.

In Tables 9 and 10, further dyestuffs which may be prepared in analogy with the procedure described in Example 98 are given.

                                      TABLE 9                                      __________________________________________________________________________      ##STR39##                                                                     Example                                                                        No.  R.sub.1                                                                             R.sub.2 R.sub.6                                                                          R.sub.6 '                                                                         R.sub.7                                                                            R.sub.12                                                                             R.sub.14                                                                           Shade on polyester                        __________________________________________________________________________      99  H    H       H H  H   Cl    NO.sub.2                                                                           blue                                      100  C.sub.2 H.sub.5                                                                     H       H Cl H   Br    "   "                                         101  H    C.sub.2 H.sub.5                                                                        H Br H   I     "   "                                         102  H    COCH.sub.3                                                                             H Cl CH.sub.3                                                                           Br    CN  "                                         103                                                                            nC.sub.4 H.sub.9                                                                    CHO  Br      H H  Br  "     "                                             104  H    H       H H  H   SO.sub. 2 CH.sub.3                                                                   NO.sub.2                                                                           "                                         105  CH.sub.3                                                                            H       H H  H   CN    CN  "                                         106  H    COC.sub.2 H.sub.5                                                                      H Cl H   SO.sub.2 CH.sub.3                                                                    "   "                                         107                                                                            nC.sub.3 H.sub.7                                                                    CH.sub.2 C.sub.6 H.sub.5                                                            H       H H  I   NO.sub.2                                                                             "                                             108  H    H       H H  H   H     CN  violet                                    109  H    H       H H  H   SO.sub.2 C.sub.6 H.sub.5                                                             NO.sub.2                                                                           blue                                      110  CH.sub.3                                                                            COCH.sub.2 Cl                                                                          H H  H   SO.sub.2 C.sub.2 H.sub.5                                                             "   "                                         111  H    CH.sub.2 CH.sub.2 OH                                                                   H H  H   SCN   "   "                                         112  C.sub.2 H.sub.5                                                                     COCH.sub.3                                                                             H Cl H   H     Cl  rubine                                    113  H    H       H H  H   I     NO.sub.2                                                                           blue                                      114  H    COCH.sub.3                                                                             H H  H   Cl    "   "                                         115  H    "       H H  H   Br    "   "                                         116  H    "       H H  H   I     "   "                                         __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________      ##STR40##                                                                     Example                               Shade on                                 No.  R.sub.1                                                                             R.sub.2                                                                               R.sub.6                                                                          R.sub.6 '                                                                         R.sub.7                                                                          D             polyester                                __________________________________________________________________________     117  H    H      H H  H                                                                                 ##STR41##    blue                                     118  H    COOCH.sub.3                                                                           H H  H                                                                                 ##STR42##    "                                        119  C.sub.2 H.sub.5                                                                     COCH.sub.3                                                                            H H  H                                                                                 ##STR43##    "                                        120  H    H      Cl                                                                               H  H                                                                                 ##STR44##    "                                        121  H    COCH.sub.2 Cl                                                                         H H  H                                                                                 ##STR45##    "                                        122  CH.sub.3                                                                            H      H Br H                                                                                 ##STR46##    "                                        123  H    H      H H  H                                                                                 ##STR47##    "                                        __________________________________________________________________________

In Table 11, further dyestuffs which may be prepared in analogy with the procedure described in Example 1 are given.

    TABLE 11       ##STR48##       Example           Shade on No. R.sub.1 R.sub.3 R.sub.3 ' R.sub.4      R.sub.2 R.sub.12 R.sub.14 R.sub.13 R.sub.10 R.sub.11 polyester        124 C.sub.2 H.sub.4OC.sub.2 H.sub.5 H H CCH CH.sub.2 CH.sub.2OCHO CN      CN NO.sub.2 Cl NHCHO blue 125 CH.sub.2 CHCH.sub.2 H H CCH  CH.sub.2      CH.sub.2OCOCH.sub.3 CHO CF.sub.3 NO.sub.2 Br       ##STR49##       red 126 CH.sub.2CHCHCl CH.sub.3 CH.sub.3 CCH CH.sub.2       CH.sub.2OCOC.sub.2 H.sub.5 SO.sub.2 CH.sub.3 SO.sub.2 CH.sub.3 NO.sub.2 C      H.sub.3 CN blue 127 CH.sub.2CClCH.sub.2 H H CCH CH.sub.2       CH.sub.2OCOC.sub.3 H.sub.7 SO.sub.2 C.sub.2 H.sub.5 SO.sub.2 CH.sub.3      NO.sub.2 C.sub.2 H.sub.5 NHCOC.sub.6 H.sub.5 blue             128      CH.sub.2 CH.sub.2C.sub.6 H.sub.5 H H CCH H I I NO.sub.2 OCH.sub.2CN       ##STR50##       brown 129      n(CH.sub.2).sub.4OCOH H H CCH H Br H SO.sub.2 NHC.sub.2 H.sub.5 OC.sub.2      H.sub.4OH       ##STR51##       red 130 H H H CCCH.sub.2OCH.sub.3 H I H SO.sub.2       NH.sub.2 H      ##STR52##       " 131 H H H CCH H COOC.sub.2 H.sub.5 H NO.sub.2 H NHCOC.sub.2       H.sub.5OCH.sub.3 " 132 C.sub.4 H.sub.8OC.sub.2       H.sub.5 H H CCH COCH.sub.3 COOCH.sub.3 H NO.sub.2 H OC.sub.2 H.sub.5      red 133 C.sub.3 H.sub.6OCOOCH.sub.3 CH.sub.3 H CCH COCH.sub.3 H H      C.sub.6 H.sub.5C.sub.6 H.sub.4NN H NHCOCH.sub.2C.sub.6 H.sub.5 red 134      C.sub.2 H.sub.4OCOOC.sub.2       H.sub.5 CH.sub.3 CH.sub.3 CCH H Cl H 4-NO.sub.2C.sub.6 H.sub.4NN H      NHCOC.sub.2 H.sub.4 C.sub.6 H.sub.5 " 135 C.sub.2 H.sub.4OCONHC.sub.2      H.sub.5 H H CCCH.sub.2 OCH.sub.3 CH.sub.3 Br H 2,4-di-NO.sub.2C.sub.6      H.sub.3NN H NHCOC.sub.2 H.sub.4OCH.sub.3 " 136 CH.sub.2CBrCH.sub.2 H H      CCH H H H 4-NO.sub.22-CNC.sub.6 H.sub.3NN H NHCOC.sub.3 H.sub.6 OC.sub.2      H.sub.5 " 137 C.sub.3 H.sub.7 H H CCH C.sub.2       H.sub.5 H H 3-CH.sub.3C.sub.6       H.sub.4NN CH.sub.3      ##STR53##       " 138 C.sub.2 H.sub.5 H H CCH H H H 2,3,5-tri-ClC.sub.6 H.sub.2NN H       ##STR54##       " 139 C.sub.4 H.sub.9 H H CCH H H H 3,4-di-BrC.sub.6 H.sub.3NN H      NHCOCH.sub.2C.sub.6 H.sub.5 " 140 C.sub.2 H.sub.4 CN H H CCH H H H      3,5-di-OCH.sub.3C.sub.6 H.sub.3NN H NHCOC.sub.2 H.sub.4 C.sub.6 H.sub.5      " 141 C.sub.2 H.sub.4 OCOCH.sub.3 H H CCH H H H 2-BrC.sub.6 H.sub.4NN H      NHCOC.sub.2 H.sub.4 Br " 142 H H H " H CN NO.sub.2 NO.sub.2 OCH.sub.3      NHCOCH.sub.3 blue    143       ##STR55##       yellow 144       ##STR56##       yellow

EXAMPLE 145

15.1 parts N-methyl-2-methoxy-5-methylaniline and 20 parts 2-hydroxy-3-chloropropyl-prop-2'-ynylether are mixed and 7 parts pulverized potassium hydroxide are added portionwise thereto whereby the temperature rises from 25° to 50°. The mixture is stirred for 10 hours at 85° and cooled to room temperature. 100 parts dilute hydrochloric acid are added thereto and the mixture is stirred for 10 minutes. The organic phase, N-methyl-N-[3-prop-2'-ynyloxy-2-hydroxypropyl]-2-methoxy-5-methylaniline, is separated out.

To 122.5 parts conc. sulphonic acid, 35 parts nitrosylsulphuric acid (40%) are added dropwise over a period of 15 minutes at a temperature of max. 20° C. At the same temperature 26.2 parts 2-bromo-4,6-dinitroaniline are added thereto over a period of 30 minutes and the whole is stirred for 6 hours at max. 20°. At 0° to 5° the solution is added to 26.3 parts of the coupling component produced above in 200 parts methanol, which solution is cooled externally. After coupling is complete 30% NaOH is added to precipitate the dyestuff. The dyestuff is filtered and washed with water until acid free.

The dyestuff obtained corresponds to the formula ##STR57## and dyes polyester by the rapid dyeing process in navy blue shades.

EXAMPLE 146

In analogous manner the dyestuff of the formula ##STR58## is produced using 30.6 parts coupling component and coupling is conducted in a mixture of 100 parts water/20 parts glacical acetic acid and 10 parts hydrochloric acid, ice being added to keep the temperature at 0° to 5°.

The dyestuff dyes polyester in blue shades.

APPLICATION EXAMPLE

7 Parts of the dyestuff produced in accordance with Example 1 are ground to a fine powder in a ball mill for 48 hours with 4 parts sodium dinaphthylmethanedisulphonate, 4 parts sodium ethylsulphate and 5 parts anhydrous sodium sulphate.

1 Part of the dyestuff preparation obtained is mixed with a little water and the suspension is added through a sieve to a dyebath containing 2 parts sodium laurylsulphate in 4000 parts water. 100 parts of scoured polyester material is added to the bath at 40°-50° C. (liquor ratio 1:40), 20 parts of chlorobenzene are added thereto, the bath is slowly heated to 100° C. and dyeing is effected for 1 to 2 hours at 95°-100° C. The dyed substrate is washed, soaped, washed again and dried. The deep blue level dyeing possesses notable light-, wash-, sublimation-, thermofixation- and permanent pressfastness.

The compounds of Examples 2 to 146 may also be employed to dye polyester in analogous manner. 

What is claimed is:
 1. A disperse dye of the formula ##STR59## wherein D is a diazo component radical, ##STR60## or 1,4-naphthylene, wherein R₁₀ is hydrogen, chloro, bromo, C₁₋₂ alkyl, C₁₋₂ alkoxy, 2-hydroxyethoxy, 2-methoxyethoxy or cyano(C₁₋₂ alkoxy), andR₁₁ is hydrogen, chloro, bromo, C₁₋₂ alkyl, C₁₋₂ alkoxy, (C₁₋₄ alkyl)carbonylamino, (C₁₋₂ chloroalkyl)carbonylamino, (C₁₋₂ -bromoalkyl)carbonylamino, cyano, formamido, (C₁₋₂ alkoxy) (C₁₋₄ alkyl)-carbonylamino, (C₁₋₄ alkoxy)carbonylamino, phenoxy(C₁₋₂ alkyl)carbonylamino, 2-(C₁₋₂ alkoxy) (C₂₋₃ -alkoxy)carbonylamino, 3-(C₁₋₂ alkoxy)propoxycarbonylamino, (C₁₋₄ alkoxy)carbonyl (C₁₋₃ alkyl)aminocarbonylamino, benzamido or phenyl-(C₁₋₂ alkyl)carbonylamino, R₁₁ being ortho to the --N═N-- radical, R₁ is hydrogen; C₁₋₆ alkyl; C₂₋₆ alkenyl; C₂₋₆ haloalkenyl; C₁₋₆ alkyl monosubstituted by halo, hydroxy, C₁₋₆ alkoxy, acyloxy, phenyl, phenoxy, cyano, C₂₋₆ alkenyloxy, C₂₋₆ alkynyloxy or (C₁₋₆ alkoxy)C₂₋₆ alkynyloxy; or C₁₋₆ alkyl substituted by hydroxy and one further substituent selected from the group consisting of halo, hydroxy, C₁₋₆ alkoxy, acyloxy, phenyl, phenoxy, cyano, C₂₋₆ alkenyloxy, C₂₋₆ alkynyloxy and (C₁₋₆ alkoxy)C₂₋₆ alkynyloxy, with the proviso that R₁ must be hydrogen, C₁₋₆ alkyl or C₂₋₆ alkenyl when K' is 1,4-naphthylene, R₂ is hydrogen, acyl, C₁₋₆ alkyl or C₁₋₆ alkyl monosubstituted by halo, C₁₋₆ alkoxy, phenyl, phenoxy, benzyloxy, hydroxy or acyloxy,each of R₃ and R₃ ' is independently hydrogen or C₁₋₆ alkyl or R₃ and R₃ ' taken together and with the carbon atom to which they are joined form a cyclohexyl ring, and R₅ is hydrogen or ##STR61## wherein each of R₈ and R₈ ' is independently hydrogen or C₁₋₆ alkyl, andR₉ is hydrogen, acyl, C₁₋₆ alkyl or C₁₋₆ alkyl monosubstituted by C₁₋₆ alkoxy, (C₁₋₆ alkoxy)C₁₋₆ alkoxy or acyloxy, with the proviso that R₅ must be hydrogen when R₃ and R₃ ' taken together and with the carbon atom to which they are joined form a cyclohexyl ring,wherein each acyl and the acyl moiety of each acyloxy is independently R--O--CO--, R--SO₂ --, R'--CO--, R'--NR"--CO-- or R'--NR"--SO₂ --, wherein R is C₁₋₆ alkyl, C₁₋₆ haloalkyl, 2-hydroxypropyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, phenyl, tolyl or benzyl, and each of R' and R" is independently hydrogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, 2-hydroxypropyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, phenyl, tolyl or benzyl, andeach halo is independently fluoro, chloro, bromo or iodo.
 2. A disperse dye according to claim 1 wherein R₁₁ is hydrogen, chloro, bromo, C₁₋₂ alkyl, C₁₋₂ alkoxy, (C₁₋₄ alkyl)carbonylamino, chloroethylcarbonylamino, bromoethylcarbonylamino, cyano, formamido, (C₁₋₂ alkoxy) (C₁₋₄ alkyl)carbonylamino, (C₁₋₄ alkoxy)carbonylamino, phenoxy(C₁₋₂ alkyl)carbonylamino, 2-(C₁₋₂ alkoxy) (C₂₋₃ alkoxyl)carbonylamino, 3-(C₁₋₂ alkoxy)propoxycarbonylamino, (C₁₋₄ alkoxy)carbonyl(C₁₋₃ alkyl)aminocarbonylamino, benzamido or phenyl(C₁₋₂ alkyl)carbonylamino, R₁₁ being ortho to the --N═N-- radical.
 3. A compound of the formula ##STR62## wherein D' is phenyl; substituted phenyl having 1 to 4 substituents each of which is independently chloro, bromo, iodo (maximum of two), cyano (maximum of two), trifluoromethyl (maximum of two), C₁₋₂ alkylsulfonyl (maximum of two), nitro (maximum of two), methyl (maximum of two), methoxy (maximum of two), formyl (maximum of one), (C₁₋₄ alkyl)carbonyl (maximum of one), (C₁₋₂ alkoxy)carbonyl (maximum of one), carbamoyl (maximum of one), (C₁₋₂ alkyl)carbamoyl (maximum of one), di-(C₁₋₂ alkyl)carbamoyl (maximum of one), phenylcarbamoyl (maximum of one), (C₁₋₂ alkyl)carbonylamino (maximum of one), phenyl (maximum of one), benzoyl (maximum of one), benzylcarbonyl (maximum of one), phenylsulfonyl (maximum of one), tolylsulfonyl (maximum of one), sulfamoyl (maximum of one), C₁₋₂ alkylsulfamoyl (maximum of one), di-(C₁₋₂ alkyl)sulfamoyl (maximum of one), thiocyano (maximum of one), phenylazo or substituted phenylazo having 1 to 3 substituents each of which is independently chloro, bromo, methyl (maximum of two), C₁₋₂ alkoxy (maximum of two), cyano (maximum of two), nitro (maximum of two) or phenyl (maximum of one) (maximum number of phenylazo and substituted phenylazo together is one); benzothiazolyl; substituted benzothiazolyl having 1 or 2 substitutents each of which is independently chloro, bromo, cyano, nitro, methyl (maximum of one), C₁₋₂ alkylsulfonyl (maximum of one), sulfamoyl (maximum of one) or thiocyano (maximum of one); benzoisothiazolyl; substituted benzoisothiazolyl having 1 or 2 substituents each of which is independently chloro, bromo, cyano, nitro (maximum of one) or C₁₋₂ alkylsulfonyl (maximum of one); thienyl; substituted thienyl having 1 to 3 substituents each of which is independently chloro (maximum of two), bromo (maximum of two), cyano (maximum of two), nitro (maximum of two), methyl (maximum of one), phenyl (maximum of one), C₁₋₃ alkyl)carbonyl (maximum of one), hydroxy (maximum of one) or methoxycarbonyl (maximum of one); thiazolyl; substituted thiazolyl having 1 or 2 substituents each of which is independently chloro, bromo, cyano, methyl (maximum of one), nitro (maximum of one) or C₁₋₂ alkylsulfonyl (maximum of one); 3-phenyl-1,2,4-thiadiazolyl-5 or 2-phenyl-1,3,4-thiadiazolyl-5, ##STR63## or 1,4-naphthylene, wherein: R₁₀ is hydrogen, chloro, bromo, C₁₋₂ alkyl, C₁₋₂ alkoxy, 2-hydroxyethoxy, 2-methoxyethoxy or cyano(C₁₋₂ alkoxy), andR₁₁ is hydrogen, chloro, bromo, C₁₋₂ alkyl, C₁₋₂ alkoxy, (C₁₋₄ alkyl)carbonylamino, (C₁₋₂ chloroalkyl)carbonylamino, (C₁₋₂ bromoalkyl)carbonylamino, cyano, formamido, (C₁₋₂ alkoxy) (C₁₋₄ alkyl)carbonylamino, (C₁₋₄ alkoxy)carbonylamino, phenoxy (C₁₋₂ alkyl)carbonylamino, 2-(C₁₋₂ alkoxy) (C₂₋₃ alkoxy)carbonylamino, 3-(C₁₋₂ alkoxy)propoxycarbonylamino, (C₁₋₄ alkoxy)carbonyl (C₁₋₃ alkyl)aminocarbonylamino, benzamido or phenyl(C₁₋₂)carbonylamino, R₁₁ being ortho to the --N═N-- radical, R₁ is hydrogen; C₁₋₆ alkyl; C₂₋₆ alkenyl; C₂₋₆ haloalkenyl; C₁₋₆ alkyl monosubstituted by halo, hydroxy, C₁₋₆ alkoxy, acyloxy, phenyl, phenoxy, cyano, C₂₋₆ alkenyloxy, C₂₋₆ alkynyloxy or (C₁₋₆ alkoxy)C₂₋₆ alkynyloxy; or C₁₋₆ alkyl substituted by hydroxy and one further substituent selected from the group consisting of halo, hydroxy, C₁₋₆ alkoxy, acyloxy, phenyl, phenoxy, cyano, C₂₋₆ alkenyloxy, C₂₋₆ alkynyloxy and (C₁₋₆ alkoxy)C₂₋₆ alkynyloxy, with the proviso that R₁ must be hydrogen, C₁₋₆ alkyl or C₁₋₆ alkenyl when K' is 1,4-naphthylene, R₂ is hydrogen, acyl, C₁₋₆ alkyl or C₁₋₆ alkyl monosubstituted by halo, C₁₋₆ alkoxy, phenyl, phenoxy, benzyloxy, hydroxy or acyloxy,each of R₃ and R₃ ' is independently hydrogen or C₁₋₆ alkyl or R₃ and R₃ ' taken together and with the carbon atom to which they are joined form a cyclohexyl ring, and R₅ is hydrogen or ##STR64## wherein each of R₈ and R₈ ' is independently hydrogen or C₁₋₆ alkyl, andR₉ is hydrogen, acyl, C₁₋₆ alkyl or C₁₋₆ alkyl monosubstituted by C₁₋₆ alkoxy, (C₁₋₆ alkoxy)C₁₋₆ alkoxy or acyloxy, with the proviso that R₅ must be hydrogen when R₃ and R₃ ' taken together and with the carbon atom to which they are joined form a cyclohexyl ring,wherein each acyl and the acyl moiety of each acyloxy is independently R--O--CO--, R--SO₂ --, R'--CO--, R'--NR"--CO-- or R'--NR"--SO₂ --, wherein R is C₁₋₆ alkyl, C₁₋₆ haloalkyl, 2-hydroxypropyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, phenyl, tolyl or benzyl, and each of R' and R" is independently hydrogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, 2-hydroxypropyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, phenyl, tolyl or benzyl, andeach halo is independently fluoro, chloro, bromo or iodo.
 4. A compound according to claim 3 whereinR₁ is hydrogen; C₁₋₄ alkyl; C₂₋₄ alkyl monosubstituted in the 2-, 3- or 4-position by chloro, bromo, hydroxy, C₁₋₂ alkoxy, formyloxy, (C₁₋₄ alkyl)carbonyloxy, (C₁₋₂ alkoxy)carbonyloxy, (C₁₋₂ alkyl)carbamoyloxy, phenoxy, phenyl, benzoyloxy or cyano; 2-hydroxy-3-chloropropyl; benzyl; allyl; 2- or 3-chloroallyl; 2- or 3-bromoallyl; 2-hydroxy-3-propargyloxypropyl or 2-hydroxy-3-(4-methoxybutyn-2-yloxy)propyl, with the proviso that R₁ must be hydrogen or C₁₋₄ alkyl when K' is 1,4-naphthylene, R₂ is hydrogen; C₁₋₄ alkyl; C₁₋₄ chloroalkyl; C₁₋₄ bromoalkyl; C₂₋₄ alkyl monosubstituted in the 2-, 3- or 4-position by C₁₋₂ alkoxy, hydroxy, phenoxy, formyloxy, (C₁₋₃ alkyl)carbonyloxy or benzyloxy; (C₁₋₄ alkyl)carbonyl; benzoyl or (C₁₋₄ alkoxy)carbonyl, each of R₃ and R₃ ' is independently hydrogen or methyl or R₃ and R₃ ' taken together and with the carbon atom to which they are joined form a cyclohexyl ring, and R₅ is hydrogen, 1-(C₁₋₂ alkoxy)C₁₋₃ alkyl, (2-methoxyethoxy)methyl, acetoxymethyl or chloropropionyloxymethyl, with the proviso that R₅ must be hydrogen when R₃ and R₃ ' taken together and with the carbon atom to which they are joined form a cyclohexyl ring.
 5. A compound according to claim 3 wherein R₁ is hydrogen; C₁₋₄ alkyl; C₂₋₄ alkyl monosubstituted in the 2-, 3- or 4-position by chloro, bromo, hydroxy, C₁₋₂ alkoxy, formyloxy, (C₁₋₄ alkyl)carbonyloxy, (C₁₋₂ alkoxy)carbonyloxy, (C₁₋₂ alkyl)carbamoyloxy, phenoxy, phenyl, benzoyloxy or cyano; 2-hydroxy-3-chloropropyl; benzyl; allyl; 2- or 3-chloroallyl; 2- or 3-bromoallyl; 2-hydroxy-3-propargyloxypropyl or 2-hydroxy-3-(4-methoxybutyn-2-yloxy)propyl, with the proviso that R₁ must be hydrogen or C₁₋₄ alkyl when K' is 1,4-naphthylene.
 6. A compound according to claim 3 wherein R₂ is hydrogen; C₁₋₄ alkyl; C₁₋₄ chloroalkyl; C₁₋₄ bromoalkyl; C₂₋₄ alkyl monosubstituted in the 2-, 3- or 4-position by C₁₋₂ alkoxy, hydroxy, phenoxy, formyloxy, (C₁₋₃ alkyl)carbonyloxy or benzyloxy; (C₁₋₄ alkyl)carbonyl; benzoyl or (C₁₋₄ alkoxy)carbonyl.
 7. A compound according to claim 3 wherein each ofR₃ and R₃ ' is independently hydrogen or methyl or R₃ and R₃ ' taken together and with the carbon atom to which they are joined form a cyclohexyl ring.
 8. A compound according to claim 3 wherein R₅ is hydrogen, 1-(C₁₋₂ alkoxy)C₁₋₃ alkyl, (2-methoxyethoxy)methyl, acetoxymethyl or chloropropionyloxymethyl.
 9. A compound according to claim 3 wherein R₁₁ is hydrogen, chloro, bromo, C₁₋₂ alkyl, C₁₋₂ alkoxy, (C₁₋₄ alkyl)carbonylamino, chloroethylcarbonylamino, bromoethylcarbonylamino, cyano, formamido, (C₁₋₂ alkoxy) (C₁₋₄ alkyl)carbonylamino, (C₁₋₄ alkoxy)carbonylamino, phenoxy(C₁₋₂ alkyl)carbonylamino, 2-(C₁₋₂ alkoxy) (C₂₋₃ alkoxy)carbonylamino, 3-(C₁₋₂ alkoxy)propoxycarbonylamino, (C₁₋₄ alkoxy)carbonyl(C₁₋₃ alkyl)aminocarbonylamino, benzamido or phenyl(C₁₋₂ alkyl)carbonylamino, R₁₁ being ortho to the --N═N-- radical.
 10. A compound according to claim 2 having the formula ##STR65## wherein D' is phenyl; substituted phenyl having 1 to 4 substituents each of which is independently chloro, bromo, iodo (maximum of two), cyano (maximum of two), trifluoromethyl (maximum of two), C₁₋₂ alkylsulfonyl (maximum of two), nitro (maximum of two), methyl (maximum of two), methoxy (maximum of two), formyl (maximum of one), (C₁₋₄ alkyl)carbonyl (maximum of one), (C₁₋₂ alkoxy)carbonyl (maximum of one), carbamoyl (maximum of one), (C₁₋₂ alkyl)carbamoyl (maximum of one), di-(C₁₋₂ alkyl)carbamoyl (maximum of one), phenylcarbamoyl (maximum of one), (C₁₋₂ alkyl)carbonylamino (maximum of one), phenyl (maximum of one), benzoyl (maximum of one), benzylcarbonyl (maximum of one), phenylsulfonyl (maximum of one), tolylsulfonyl (maximum of one), sulfamoyl (maximum of one), C₁₋₂ alkylsulfamoyl (maximum of one), di-(C₁₋₂ alkyl)sulfamoyl (maximum of one), thiocyano (maximum of one), phenylazo or substituted phenylazo having 1 to 3 substituents each of which is independently chloro, bromo, methyl (maximum of two), C₁₋₂ alkoxy (maximum of two), cyano (maximum of two), nitro (maximum of two) or phenyl (maximum of one) (maximum number of phenylazo and substituted phenylazo together is one); benzothiazolyl; substituted benzothiazolyl having 1 or 2 substituents each of which is independently chloro, bromo, cyano, nitro, methyl (maximum of one), C₁₋₂ alkylsulfonyl (maximum of one), sulfamoyl (maximum of one) or thiocyano (maximum of one); benzoisothiazolyl; substituted benzoisothiazolyl having 1 or 2 substituents each of which is independently chloro, bromo, cyano, nitro (maximum of one) or C₁₋₂ alkylsulfonyl (maximum of one); thienyl; substituted thienyl having 1 to 3 substituents each of which is independently chloro (maximum of two), bromo (maximum of two), cyano (maximum of two), nitro (maximum of two), methyl (maximum of one), phenyl (maximum of one), (C₁₋₃ alkyl)carbonyl (maximum of one), hydroxy (maximum of one) or methoxycarbonyl (maximum of one); thiazolyl; substituted thiazolyl having 1 or 2 substituents each of which is independently chloro, bromo, cyano, methyl (maximum of one), nitro (maximum of one) or C₁₋₂ alkylsulfonyl (maximum of one); 3-phenyl-1,2,4-thiadiazolyl-5 or 2-phenyl-1,3,4-thiadiazolyl-5, ##STR66## or 1,4-naphthylene, wherein R₁₀ is hydrogen, chloro, bromo, C₁₋₂ alkyl, C₁₋₂ alkoxy, 2-hydroxyethoxy, 2-methoxyethoxy or cyano(C₁₋₂ alkoxy), andR₁₁ is hydrogen, chloro, bromo, C₁₋₂ alkyl, C₁₋₂ alkoxy, (C₁₋₄ alkyl)carbonylamino, (C₁₋₂ chloroalkyl)carbonylamino, (C₁₋₂ bromoalkyl)carbonylamino, cyano, formamido, (C₁₋₂ alkoxy)(C₁₋₄ alkyl)carbonylamino, (C₁₋₄ alkoxy)carbonylamino, phenoxy(C₁₋₂ alkyl)carbonylamino, 2-(C₁₋₂ alkoxy)(C₂₋₃ alkoxy)carbonylamino, 3-(C₁₋₂ alkoxy)propoxycarbonylamino, (C₁₋₄ alkoxy)carbonyl(C₁₋₃ alkyl)aminocarbonylamino, benzamido or phenyl(C₁₋₂ alkyl)carbonylamino, R₁₁ being ortho to the -N═N- radical, R_(1a) is hydrogen; C₂₋₄ alkyl; C₂₋₄ alkenyl; C₂₋₄ alkyl monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, acyloxy, phenyl, phenoxy, cyano, C₂₋₆ alkynyloxy or (C₁₋₆ alkoxy)C₂₋₆ alkynyloxy; or C₂₋₄ alkyl substituted by hydroxy and one further substituent selected from the group consisting of halo, hydroxy, C₁₋₄ alkoxy, acyloxy, phenyl, phenoxy, cyano, C₂₋₆ alkynyloxy or (C₁₋₆ alkoxy)C₂₋₆ alkynyloxy, with the provisos that R_(1a) may be C₂₋₄ alkenyl only when K' is 1,4-naphthylene and R_(1a) must be hydrogen, C₂₋₄ alkyl or C₂₋₄ alkenyl when K' is 1,4-naphthylene, R_(2a) is hydrogen, acyl, C₁₋₆ alkyl or C₁₋₆ alkyl monosubstituted by halo, C₁₋₄ alkoxy, phenoxy, phenyl, benzyloxy or acyloxy,each of R₃ " and R₃ "' is independently hydrogen or C₁₋₄ alkyl or R₃ " and R₃ '" taken together and with the carbon atom to which they are joined form a cyclohexyl ring, and R₅ is hydrogen or ##STR67## wherein each of R₈ and R₈ ' is independently hydrogen or C₁₋₆ alkyl, andR₉ ' is hydrogen, acyl, C₁₋₆ alkyl or C₁₋₆ alkyl monosubstituted by C₁₋₆ alkoxy, acyloxy or (C₁₋₄ alkoxy)C₂₋₄ alkoxy, with the proviso that R₅ must be hydrogen when R₃ " and R₃ "' taken together and with the carbon atom to which they are joined form a cyclohexyl ring,wherein each acyl and the acyl moiety of each acyloxy is independently R--O--CO--, R--SO₂ --, R'--CO--, R'--NR"--CO-- or R'--NR"--SO₂ --, wherein R is C₁₋₆ alkyl, C₁₋₆ haloalkyl, 2-hydroxypropyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, phenyl, tolyl or benzyl, and each of R' and R" is independently hydrogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, 2-hydroxypropyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, phenyl, tolyl or benzyl, and each halo is independently fluoro, chloro, bromo or iodo.
 11. A compound according to claim 9 wherein R₂ is hydrogen, C₁₋₆ alkyl or C₁₋₆ alkyl monosubstituted by halo, C₁₋₆ alkoxy, phenyl, phenoxy, benzyloxy, hydroxy or acyloxy.
 12. A compound according to claim 9 wherein D' is phenyl or substituted phenyl having 1 to 4 substituents.
 13. A compound according to claim 12 wherein D' is phenyl or substituted phenyl having 1 to 3 substituents.
 14. A compound according to claim 13 wherein D' is phenyl or substituted phenyl having 1 to 3 substituents each of which is independently chloro (maximum of two), bromo (maximum of two), iodo (maximum of two), nitro (maximum of two), cyano (maximum of two), C₁₋₂ alkylsulfonyl (maximum of two), (C₁₋₂ alkoxy)carbonyl (maximum of one), sulfamoyl (maximum of one) or di-(C₁₋₂ alkyl)sulfamoyl (maximum of one).
 15. A compound according to claim 14 wherein D' is ##STR68## wherein R₁₂ is hydrogen, chloro, bromo, iodo, nitro, cyano, C₁₋₂ alkylsulfonyl or (C₁₋₂ alkoxy)carbonyl,R₁₃ is nitro, sulfamoyl or di-(C₁₋₂ alkyl)sulfamoyl, R₁₄ is hydrogen, chloro, bromo, iodo, cyano or C₁₋₂ alkylsulfonyl, and R₁₄ ' is hydrogen, chloro or bromo, with the proviso that at least one of R₁₄ and R₁₄ ' is hydrogen.
 16. A compound according to claim 15 whereinR₁ is hydrogen, C₁₋₂ alkyl or C₂₋₃ alkyl monosubstituted in the 2- or 3-position by (C₁₋₂ alkyl)carbonyloxy or cyano, with the proviso that R₁ must be hydrogen or C₁₋₂ alkyl when K' is 1,4-naphthylene, P1 R₂ is hydrogen or C₁₋₄ alkyl, andeach of R₃ and R₃ ' is independently hydrogen or methyl.
 17. A compound according to claim 16 whereinR₃ is hydrogen, and R₃ ' is hydrogen.
 18. A compound according to claim 16 wherein R₅ is hydrogen, (2-methoxyethoxy)methyl or acetoxymethyl.
 19. A compound according to claim 15 whereinR₁₂ is nitro or cyano, R₁₃ is nitro, R₁₄ is chloro, bromo, cyano or methylsulfonyl, and R₁₄ ' is hydrogen.
 20. A compound according to claim 19 whereinR₁ is hydrogen, R₂ is hydrogen, andwherein R₅ " is hydrogen, (2-methoxyethoxy)methyl or acetoxymethyl.
 21. A compound according to claim 3 having the formula ##STR69## wherein R₃₀ is C₁₋₂ alkyl, 2-methoxyethyl or 2-hydroxyethyl, andR₃₁ is hydrogen, C₁₋₂ alkyl, chloromethyl, (C₁₋₂ alkoxy)C₁₋₄ alkyl or C₁₋₄ alkoxy, R₂ "' is hydrogen or acetyl, R₁₂ ' is nitro or cyano, and R_(14a) is chloro, bromo, iodo, cyano or methylsulfonyl.
 22. A compound according to claim 21 having the formula ##STR70## wherein R_(14a) ' is chloro, bromo or iodo,R₃₀ ' is methyl or ethyl, and R₃₁ ' is methyl or ethyl.
 23. The compound according to claim 22 having the formula ##STR71##
 24. The compound according to claim 21 having the formula ##STR72##
 25. The compound according to claim 19 having the formula ##STR73##
 26. The compound according to claim 21 having the formula ##STR74##
 27. The compound according to claim 20 having the formula ##STR75##
 28. The compound according to claim 21 having the formula ##STR76##
 29. The compound according to claim 21 having the formula ##STR77##
 30. The compound according to claim 21 having the formula ##STR78##
 31. The compound according to claim 21, having the formula ##STR79## 